Returning to NYC, Kennedy landed another understudy gig, this time to Emily Skinner as Daisy in the 1997 musical "Side Show", a fictionalized biography of the conjoined twins Daisy and Violet Hilton. (Ironically, Alice Ripley was cast as Violet and Kennedy went on for Skinner on over 30 occasions during the musical's brief run.) The performer remained active in regional theater productions and working on demo recordings. In 2000, she was teamed with Karen Mason (Glenn Close's understudy in "Sunset Boulevard") in the stage musical adaptation of Irving Berlin's "White Christmas". Kennedy then created the lead role of Petra, a vocalist in a 1930s German swing band, whose relationship with a Jewish musician is threatened by the rise of the Nazis in the new musical "The Rhythm Club", which premiered at the Signature Theatre in Arlington, Virginia.